House vacation rentals in Downtown Chicago

Cool Quiet Coach House, Private Access + Patio

Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.

Large Home | Free Parking | Near Downtown

• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

NEW! 3BR/2.5B Duplex in Noble Sq

Welcome to our stunning 3 bedroom, 2.5 bath duplexed condo with free parking and ample outdoor space in the heart of the vibrant Noble Square neighborhood. This open, bright and spacious unit is a true urban oasis that will make you feel right at home in the epicenter of Chicago. Our condo is close to some of the city's best restaurants, cafes, and bars, as well as several beautiful parks. With its unbeatable location, modern design, luxurious amenities, and SuperHost service - look no further!

Charming 3-BED in Lincoln Park/ Old Town & Parking

Welcome to our charming retreat in the historic Old Town Triangle/Lincoln Park district of Chicago. This conveniently located 3-bedroom apt, including office space, is nestled in the heart of a safe residential neighborhood with a 5-min walk to Brown Line and 10-min to Red Line. Within a 20-min walk, you'll find yourself at Lincoln Park Zoo, Beach, Second City, and Wells Street, immersing yourself in the vibrance of the old town. Book now to experience the best of Chicago. Parking+EV charging.

Luxury SOHO Styled Two-Level Townhouse - Old Town

NEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN! This private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

*Due to AirBnB new changes in fee disclosure, 18% of the daily rate you see goes to Airbnb* 1 King, 1 Queen, 1 Sofa Bed, 2 Air Mattresses (2 Queens) 1 Pack n Play Enjoy your stay in this cozy modern home that sits on an oversized lot with luxury amenities and a spacious front yard. A parking space in the rear allows parking for 2 cars. The ideal getaway to grill up some food and relax in the jacuzzi hot tub year round! We are pet friendly! Please reach out with any questions. NO CHORES!

Architect's Urban Oasis | 4bd/3ba I Luxe

Experience our one-of-a-kind home in the heart of downtown Chicago. It has 4 bedrooms, 3 bathrooms and comfortably sleeps 8. We are offering our home to select people visiting Chicago. Perfect for families and mature groups. I am an architect, and designed this home for my family in 2005. It was published in Chicago Magazine, Playboy, and featured in several TV commercials. Chosen by CS as the most luxurious AirBnb in Chicago in 2023. STRICT NO PARTY, EVENTS or EXTRA GUESTS policy.

Sophisticated Twnhm in Prestigious Lincoln Park

Welcome to our awesome townhome, nestled in a peaceful residential neighborhood, offering both convenience and serenity. Located with easy access to public transportation, you can explore all that Chicago has to offer. There are multiple levels to this townhome with stairs. A bedroom and bathroom on the ground floor, kitchen and living/dinning room on the middle floor, and the master bedroom with master bathroom on the top floor. A mini roof top to enjoy Chicago nights as well.

Amazing Penthouse: Views, Hot Tub, Cold Plunge!

Experience city living in this stylish 3BD/3BA duplex penthouse in the heart of Wicker Park! Just a 2-minute walk to the Damen Blue Line, top restaurants, bars, boutiques, and live music. Explore the neighborhood by day, then unwind with skyline views from two private decks, soak in the hot tub, cool off in the cold plunge, or gather around the fire pit. With three king bedrooms, two living rooms, a chef's kitchen, and a private elevator, this is city living at its finest.

Rooftop Skyline | 5 Ensuites | Games | DT 14 mins

The Monticello ~ Rooftop deck, skyline views, game room, 5 bedrooms w. ensuite bath! ★ "Beautiful, well appointed, and has thoughtful details." ☞ Fully equipped + stocked kitchen ☞ Game room w/ mini ping pong and board games ☞ Dedicated workspace + 1 Gig WiFi ☞ Parking → secured garage (2 cars) ☞ Indoor electric fireplace ☞ Multiple smart TVs (5) ☞ 3 separate bar areas 14 mins → Downtown Chicago 22 mins → Chicago Midway Airport ✈ 25 mins → Chicago O'Hare Airport ✈

Division St Designer Home In Heart of Wicker Park

Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).